


My Dummy Valentine

by Nepenthene



Category: Supernatural
Genre: Background Case, Bisexual Dean Winchester, Cas has obviously been watching romcoms, Castiel and Dean Winchester Being Idiots, Diners, F/M, Fluff, Flustered Dean Winchester, Getting Together, Gift Giving, Human Castiel (Supernatural), Idiots in Love, M/M, Matchmaker Sam Winchester, Motels, Oblivious Dean Winchester, Post-Season/Series 09 AU, Sam Winchester is So Done, This is quick and dirty don't judge, Valentine's Day, romcom vibes
Language: English
Status: Completed
Published: 2021-02-16
Updated: 2021-02-16
Packaged: 2021-03-17 17:55:05
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,297
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29475816
Author URL: https://archiveofourown.org/users/Nepenthene/pseuds/Nepenthene
Summary: Cas is, understandably, curious about Valentine's Day. Dean is being intentionally ignorant and even more of an idiot than usual.And Sam... Sam is more than ready to be an official third wheel. So when an opportunity presents itself, you can bet he's gonna take advantage of it.
Relationships: Castiel & Dean Winchester & Sam Winchester, Castiel/Dean Winchester
Comments: 12
Kudos: 111





	My Dummy Valentine

**Author's Note:**

  * For [InkOfEmrys](https://archiveofourown.org/users/InkOfEmrys/gifts), [BloodFreak47](https://archiveofourown.org/users/BloodFreak47/gifts), [MagicLia16](https://archiveofourown.org/users/MagicLia16/gifts).



> Is this late? Yes. Do I care? No. However, I had a blast writing it, and I hope y'all enjoy! I really can't get over Sam being a sneaky lil bitch and trying to matchmake his brother and his best friend.

_January 23rd_

_Broken Bow, NE_

“What is this… thing?”

Sam turns away from the sad selection of fruit the convenience store has to offer, a splotchy banana still in hand. Cas is holding a polyester teddy bear with a satiny red heart clamped between its fluffy pink paws, staring at it in consternation. Sam grins. 

“It’s just Valentine’s Day stuff, Cas. Gift bears are pretty popular.”

Cas pokes at the heart. “But Valentine’s Day isn’t until February. And stuffed animals are typically for children.” A crackly version of “I Will Always Love You” erupts from the bear after a particularly insistent poke, and Cas jumps. Sam bites back a laugh. 

“I mean, yeah, I guess. It’s just kinda something people do. Love makes you do stupid stuff, Cas, up to and including buying your girlfriend a shitty stuffed bear. Believe me.”

Cas nods, considering that statement carefully. He strokes the bear’s head. Sam smiles and exchanges his banana for some orange juice. 

Dean wanders over, a bag of chips in hand. He peers at the bear. “Jesus, Valentine’s Day shit already? It’s not even February yet.”

Cas presses the button again and shows Dean the bear. “It sings Whitney Houston.” He pauses, then adds, “And it’s soft.”

Dean raises an eyebrow. “You like this thing? It’s a gimmick, Cas. The capitalist machine pullin’ you in.” 

Cas shrugs. “It does seem slightly premature, but I understand the draw.” He reluctantly puts the bear back on the pile and drops a packet of dried mangoes into Sam’s basket. “I’ll wait in the car.”

Sam pays for his stuff and leaves Dean to finish picking out his junk food, strolling out to the car and sliding into the passenger seat. It’s still pretty cool out, and he’s glad he remembered to wear a heavier jacket. He’d thought he was gonna have to remind Cas, but Dean had already gotten him all set up with one of his coats before they left. 

He’s handing Cas his mangoes when he realizes that the bear is probably just the first instance of many, many future interrogations about the intricacies of Valentine’s Day. This’ll be Cas’ first one since he Fell, and he’s probably gonna have a shitload of questions. Most of which Sam knows he’s probably gonna end up answering. Dean’s been good about humouring Cas’ curiosity up to this point, _really_ good, but his patience only extends so far, and talking about Valentine’s Day definitely shortens that marker by a long shot. As far as Dean’s concerned, the only good thing about it is the plethora of hopeful women that haunt the bars. That, and the discount chocolate afterwards. 

Dean gets into the car, his plastic bag crinkling loudly in his hand. He rummages around for a second, then pulls out one of those god awful bears and twists around in his seat to hand it to Cas. 

“Here. Happy really-fuckin’-early Valentine’s Day.”

Cas smiles at Dean in mild bemusement. “I thought you said these were a gimmick.”

Dean snorts. “Uh, yeah. But they’re hilarious, so. Consider it a reminder of the evils of our society or somethin’. Enjoy.”

Cas does. Whitney crackles from the back seat as they pull out of the convenience store parking lot, and Sam notices Dean’s mouth twitch into a tiny, pleased smile, his eyes on the rearview mirror.

 _Huh_ , Sam thinks. _Interesting_. 

_February 5th_

_Oskaloosa, IA_

Sam’s just taken the last bite of his pancakes when Cas lays his paper flat on the table and points at an ad. “Do people still use these advertisements?”

Sam leans across the table and Dean spares the paper a sideways glance, both of them reading the swirly red script. Dean rolls his eyes. “Nah, man,” he drawls, nudging Cas with his elbow. “People barely even read newspapers anymore. That kind of sentimental shit only goes down in rom-coms.” 

Cas cocks his head. “I take it you regard these things the same way you do those gift bears.”

Dean snorts, drizzling more syrup on his pancakes. “Sure. But this isn’t even funny. This is just sad.” Then he flips Sam off in response to the judgmental eyebrow he’d raised at the lake of syrup on his plate, and picks up his utensils back up. Sam surreptitiously moves the syrup to the opposite end of the table.

“It’s more of the same, Cas. Some people think that sorta thing’s romantic, y’know? Tell someone you love ‘em with a big confession in the paper, leave a message for your partner. You gotta remember, Dean’s just a bitter asshole about Valentine’s Day in general.”

Dean points a pancake-laden fork at Sam. “Damn right. But I’m not gonna lie,” he says as he takes a bite, “th’ chocl’t s’les aft’r r’ gread.”

Cas and Sam exchange looks of mild disgust, and Dean grins smugly, cheeks puffed out like a chipmunk. Cas takes a thoughtful sip of his coffee. “So you wouldn’t appreciate it if I placed a message there expressing how much I value our friendship, Dean?”

Dean chokes, nearly spewing his mouthful of pancake all over the table. Sam stifles a laugh, because the careful innocence in Cas’ face means he’s _definitely_ being obtuse on purpose. Dean struggles to swallow his pancakes, fixing Cas with a horrified look, his face red. Sam doesn’t think it’s only because of all the pancake he just inhaled, either.

“What the— no, Cas! That’s not— you don’t—”

Cas tilts his head. “I don’t what?” Then he grins, and Dean elbows him in the arm, going from embarrassed tomato to angry tomato in roughly two seconds flat as he realizes Cas is fucking with him. Cas just smiles wider in satisfaction and awkwardly accepts Sam’s fist-bump. Dean tosses his utensils onto his almost empty plate.

“Yeah, yeah, hilarious. Laugh it up, fuckers. Last time I fall for that bullshit, I swear.”

Sam fishes enough twenties out of his wallet to settle the bill and stands up, still smiling. “Sure, Dean. C’mon, we gotta get going. Those witnesses aren’t gonna interview themselves.”

Dean’s still grumbling about his pancakes when they head out, and doesn’t stop for the rest of the day, but they actually do manage to get some good information out of the two women they talk to. It’s definitely a ghost; salt n’ burn tonight, and they’ll be on their way home tomorrow.

He brings the whole Valentine’s ad thing up again, though. He starts trying to explain, out of the blue, why it’d be weird for Cas to put something in there about him, and it quickly turns into the conversational equivalent of a car wreck. Sam couldn’t look away if he tried. Cas squints at Dean in confusion as he fumbles his way towards a convoluted point, flustered stuttering and erratic hand-waving everywhere. When his increasingly incoherent rambling finally peters off into an awkward, embarrassed silence, Cas abruptly changes the subject to ask Sam about a slight discrepancy between the witness’ stories. Dean, in the chair in the corner, crosses his arms and slumps down in his seat. The tips of his ears are red.

As he slowly starts to answer Cas’ question, Sam files the odd reaction away in the same mental folder as the teddy bear debacle, and he wonders.

Maybe... maybe something’s finally changing. Maybe Dean’s slowly coming towards some kind of revelation.

If this is how he’s doing it, though… 

God help them all. This is gonna be _painful._

_February 14th_

_Lebanon, KS_

Sam puts his headphones on, keying up Netflix on his laptop, and settles back into his pillows as the intro music for the new episode of _Making A Murderer_ starts piping into his ears. But the intro has barely finished when something smacks his shoulder. He jumps, looking up to see Dean lounging in the doorway of his room. Sam sighs and hits pause, chucking the balled-up sock back at his brother. “What?”

Dean grins. “Just wanted to know if you had any special requests for dinner tonight. Chef Dean’s feelin’ creative.”

Sam quirks an eyebrow in confusion. “Uh, really? I thought you’d be going out later.”

“No. It’s a Tuesday, dude,” Dean says, looking at him oddly. “I know you think I’ve got a problem, but damn. I don’t have _that_ much of a problem.”

Okay, something’s really up. “Right. But it’s Valentine’s Day.”

Dean’s lounge becomes performatively relaxed as he tries to avoid looking shifty. He fails. Dismally. “Yeah, I dunno. Just not feelin’ it, I guess.” He crosses his arms. “Well? You got suggestions, or what?”

Sam shakes his head. “Uh, I guess that carbonara you made a couple weeks ago was good. What about that?”

“Sure, good idea. I wanted to tweak that a little anyways. Can you run down to the store and get some bacon, a baguette, and, uh... whipping cream for me? I’ve got a pie in the oven already, I’ve gotta keep an eye on it.”

Sam sighs, closing his laptop regretfully. This is gonna be worth it, though, so he supposes _Making A Murderer_ can wait. “Fine. I’ll be back in a bit.”

— - —

Unsurprisingly, the grocery store is pretty much a ghost town. Sam grabs Dean’s stuff in no time, and since it’s not that late yet, he parks outside his favourite cafe and wanders in to get something to drink before heading back to the Bunker. They’ve got a spread of nauseating-looking Valentine’s drinks, but there’s a matcha latte there he’s never seen before, so he orders one of those from the pretty barista and moves along to the end of the counter.

He tugs a copy of the Lebanon Herald over, flipping through it while he waits. The Valentine’s classifieds catch his attention, and he remembers Dean’s weirdness in Iowa with a rueful shake of his head. He’s not gonna lie, most of these messages _are_ pretty cringe-inducing, yeah, but a couple are actually kinda sweet.

He’s halfway down the page when he stops, his mouth dropping open in shock. He snatches the paper up to get a better look at the short message, eyes wide.

“Sam? Matcha latte for Sam?”

He looks up from the paper, taking his drink from the barista. “Thanks. Uh, would you mind if I took this?” he asks, giving the paper a little waggle. “I can pay for it.”

The barista shakes her head, a couple of the few dark curls escaping from her bun bouncing cheerily as she waves him off. “No, go ahead. It’d just go right into the recycling, anyways.” She smiles, a small twinkle in her eye. “If you’re set on paying, though, you could just promise to come back. I work the morning shift, most days. My name’s Ashley.”

Sam blinks. Then a tiny grin pulls at his mouth. “That’s… uh, that’s good to know. I’ll, uh. See you around, then.”

She raises an eyebrow. “I hope so. Have a nice day.”

He thinks it must say something about Ashley that he doesn’t even remember why he wanted the paper so bad until he’s halfway back to the Bunker. But even getting flirted with can’t distract him from the solution to his years of not-actually-third-wheeling for long.

Now, Sam’s under no illusions; he knows that if the plan slowly forming in his head works, all he’ll be doing is plain old third-wheeling. But honestly, he’ll take it. He might regret saying this later, but he’d take gross, overt PDA over the usual infuriating UST any day. 

And Dean… Dean deserves something good. God knows he’s given enough, sacrificed enough. _More_ than enough, even if he doesn’t see it that way. Everyone else does, though, and it’s high time he gets his head out of his ass enough to see that they’re right. 

Sam’s ready, he’s willing, and he’s gonna do whatever it takes.

It’s time to break Dean’s brain.

— - —

Dinner, if Dean says so, was a success.

He’d been worried, for a little while there, that Sam was gonna try to pull a Freud and psychoanalyze his sudden lack of interest in heading out to snag a hookup. Hell, he’d freaked _himself_ out earlier when he realized he didn’t really wanna go out. He didn’t dare consider _why_ that was, though; all he was willing to admit to himself was that staying in, making some good food, and then maybe hanging out on the couch with Cas watching a movie sounded _way_ better than his usual schtick. Like. So much better it’s stupid.

So… that’s what he decided he’d do, and so far it’s working out great. Cas liked the pie Dean made as much as he did last time, Sam was sufficiently distracted by the carbonara, and now they’ve split off on their own for a bit before reconvening in the den. ‘They’ being just Cas and Dean, though. Sam had said something about watching his stupid true crime shows instead, so he’ll probably retreat to his room for that.

As he walks into the library, Dean wonders idly if he’s got half a chance of convincing Cas to watch Tombstone again.

Sam’s sitting at one of the tables, his almost-empty beer from dinner next to him as he reads a newspaper. 

“What’s that?” Dean asks, peering over Sam’s shoulder.

“Paper from town,” Sam replies absently, flipping a page. “You should take a look at the Valentine’s page, actually. There’s some pretty funny shit in here.”

Dean shakes his head, chuckling, and heads over to pour himself a glass of whiskey. “Yeah? What kinda stuff? Are we talkin’ sappy, chick-flick, or straight up gross?”

Sam doesn’t reply, though. Dean turns around, glass in hand, and frowns in confusion. “Sam?”

He’s… gone? He’s gone. He left. The guy just up and fucked off on him.

Dean shakes his head, baffled. What a weirdo. He left his paper here, though, and Dean takes a sip of his whiskey as he stops next to the table, looking down at it. It’s open to the Valentine’s page, and he snorts at the ridiculous things people’ve written, everything from bad poetry to what looks like a spoof of _Love Me Tender._ There’s even a marriage proposal. Seriously, guys. Just no. 

Then something catches his eye, and he does a double take. He freezes, his entire body going stiff and tense. 

That’s his name. 

He carefully puts down his glass and picks up the paper, not quite believing what he’s seeing. 

HELLO DEAN.

Human feelings are still strange and overwhelming,

but truthfully, I have not been confused about what

I feel for you for a long time. There is no other place

in the universe I would rather be than by your side.

\- Castiel

Cas _knows_ what putting a message here implies. They _explained_ it to him. 

Does—

Does that mean that— 

That _Cas—_

The soft pad of footsteps on the stairs jolts Dean out of his daze, and Cas smiles at him as he walks over, a couple books tucked under his arm. He’s wearing one of Dean’s old t-shirts.

“Cas. What’s this.”

The guy stays remarkably calm, considering Dean was probably never supposed to see this. He leans in to read the message Dean’s pointing to, the one that _he_ wrote (what the fuck what the fuck what the _fuck),_ and deliberately puts his book down on the table. He doesn’t seem embarrassed, but he isn’t looking at Dean, either. “It’s a Valentine’s Day message board. You pay a small fee to have a message of your choosing appear in the February 14th issue of the Lebanon Herald.”

 _Jesus fucking—_ “I know that. What I want to know is why there’s a message on here from you to me.”

Cas’ fingers find a hole in the hem of his shirt, plucking at the worn fabric. “I don’t want to make you uncomfortable.”

Dean just waits. Cas looks Dean in the eyes, searching for any hint of a way out. There is none. 

Finally, he sighs, forcing the words out like he’s pulling teeth. “Since I Fell, things have been... different. I’m going to die one day. That was always a possibility, but the odds of that day coming sooner rather than later are much higher now than they were when I was an angel.”

Dean frowns at the thought. “Not if I can help it,” he mumbles.

That makes a soft, tender expression flit across Cas’ face, and Dean feels himself flush. But then his face closes off, back into the grudging, secretive mask it was before. “You… you’ll think its foolish. I don’t… we don’t need to talk about this. We can throw the paper out. Just ignore it, you’re good at that.”

Dean’s practically vibrating with frustration. And anticipation, and terror, and _hope._ “Jesus— Cas, just. _Tell me._ Why. Did you. _Do_ that.”

A spark of defiance lights in his eyes and he straightens up, getting all up in Dean’s space. “Because I love you, Dean,” he hisses. “And I needed to say it to _someone_ before I died, even if that someone wasn’t you. That’s it. That’s why. Are you happy?”

He.

Dean is.

_What._

Meanwhile, Cas is working himself up into one of his blazing angelic furies in the face of Dean’s mute shock. “I know you don’t reciprocate. I’ve made my peace with that. But I have hidden this for far too long, and I am finished. I’m done, Dean. I love you and I will not be ashamed of it.”

He stands in front of Dean with his hands balled into fists, in his hand-me-down clothes and his messy hair, his eyes flashing and his mouth screwed up into a defiant line. And he is the most incredible thing Dean has ever seen in his whole goddamn life.

Finally, Dean manages to swallow and takes a deep, shuddery breath. “Cas?”

“Yes?”

“You’re an idiot.” And before Cas can do anything more than open his mouth to retaliate, Dean steps forward and kisses him. 

Cas’ stubble is rough against his thumbs, the skin of his neck soft and warm under Dean’s palms. It takes Cas a few heart-stopping seconds to kiss him back, but when he does... Dean can’t remember the last time he was this happy.

It’s not a long kiss, or even a really good one, technically speaking. There’s too much desperation in it, too many heightened emotions. But when they break apart, only far enough to take a breath, Dean can’t stop smiling for the life of him. 

“I, uh... me too. I’m an idiot. And the, uh. The other thing. That too.”

Cas’ hands tighten slightly on Dean’s hips. “I… yes. I gathered.”

They stand there, staring into each other’s eyes. And Dean doesn’t think Cas has the first idea where to go from here either.

The reality of what just happened starts to sink in, though, and Dean’s heart rate speeds up. And not in a good way. In a decidedly bad, ‘oh shit’ kinda way. He gulps. 

“Cas.”

Cas blinks. “Yes?”

“If you don’t kiss me again right now I’m gonna freak the fuck out.”

Thankfully, Cas can be one hell of a distracting guy when he feels like it. And judging by the way he backs Dean against a bookshelf, dragging his teeth over Dean’s lower lip, he _definitely_ feels like it.

Yeah. There’s no way they’re gonna get around to that movie.

— - —

Sam hits pause, lifting one side of his headphones off his ear. He's pretty sure he heard something over the creepy music of his documentary. Something from Dean’s end of the hall.

Shuffling, a snatch of low, indistinct speech. What sounds disturbingly like a strangled little sigh.

Then the firm slam of a door.

Sam grins, turns up the volume, and hits play again.

**Author's Note:**

> So as I'm sure you're aware, Dean and Cas just got married yesterday. I have been having... many thoughts. So if a wedding fic shows up in the next few months, I wouldn't be surprised at all. 
> 
> Hope you all had a great Valentine's Day! Consider this a little gift from me to you. ;)


End file.
